A One-Pot, Single-Solvent Process for Tandem, Catalyzed C-H Borylation-Suzuki-Miyaura Cross-Coupling Sequences

被引：49

作者：

Harrisson, Peter ^{[1
]}

Morris, James ^{[2
]}

Steel, Patrick G. ^{[1
]}

Marder, Todd B. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Jealotts Hill Int Res Ctr, Syngenta Ltd, Bracknell RG42 6EY, Berks, England

来源：

SYNLETT | 2009年 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

biaryls; cross-coupling; homogeneous catalysis; boronate ester; tandem reactions; 1,3-DISUBSTITUTED ARENES; COMPLEXES; PINACOLBORANE; ROUTE;

D O I：

10.1055/s-0028-1087374

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl tert-butyl ether is a Suitable solvent for iridium-catalyzed C-H borylation followed, in the same pot, by palladium-catalyzed Suzuki-Miyaura cross-coupling sequences, giving high yields of biaryls.

引用

页码：147 / 150

页数：4

共 26 条

[1] Microwave-assisted aqueous Suzuki cross-coupling reactions [J].

Blettner, CG ;

König, WA ;

Stenzel, W ;

Schotten, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3885-3890

[2] Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation [J].

Boebel, Timothy A. ;

Hartwig, John F. .

TETRAHEDRON, 2008, 64 (29) :6824-6830

[3] Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates [J].

Chan, DMT ;

Monaco, KL ;

Li, RH ;

Bonne, D ;

Clark, CG ;

Lam, PYS .

TETRAHEDRON LETTERS, 2003, 44 (19) :3863-3865

[4] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine [J].

Chen, G ;

Tokunaga, N ;

Hayashi, T .

ORGANIC LETTERS, 2005, 7 (11) :2285-2288

[5] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[6] Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters [J].

Coventry, DN ;

Batsanov, AS ;

Goeta, AE ;

Howard, JAK ;

Marder, TB ;

Perutz, RN .

CHEMICAL COMMUNICATIONS, 2005, (16) :2172-2174

[7]

Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548

[8] One-pot borylation/amination reactions: Syntheses of arylamine boronate esters from halogenated arenes [J].

Holmes, D ;

Chotana, GA ;

Maleczka, RE ;

Smith, MR .

ORGANIC LETTERS, 2006, 8 (07) :1407-1410

[9] Transition metal-catalyzed borylation of alkanes and arenes via C-H activation [J].

Ishiyama, T ;

Miyaura, N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) :3-11

[10] Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent [J].

Ishiyama, T ;

Nobuta, Y ;

Hartwig, JF ;

Miyaura, N .

CHEMICAL COMMUNICATIONS, 2003, (23) :2924-2925

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